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Molecular Studies of Natural Compounds and Plant Extracts

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A special issue of International Journal of Molecular Sciences (ISSN 1422-0067). This special issue belongs to the section "Bioactives and Nutraceuticals".

Deadline for manuscript submissions: closed (31 December 2023) | Viewed by 12608

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Prof. Dr. Diamanto Lazari

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Laboratory of Pharmacognosy, School of Pharmacy, Faculty of Health Science, Aristotle University of Thessaloniki, 541 24 Thessaloniki, Greece
Interests: medicinal and aromatic plant; bioactive compounds; chromatography; spectroscopy; antioxidant activity; phenolic compounds; bioactivity; chemistry of natural substances; isolation, structural determination, characterization and biological evaluation of potentially interesting; secondary metabolites for pharmaceutical; alimentary and cosmetic fields; food chemistry; essential oils from aromatic plants
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Special Issue Information

Dear Colleagues,

This Special Issue highlights the growing interest in active molecules found in plant extracts and their applications. Plant extracts are widely used in food, health supplements, and medicines, due to the presence of natural nutrients and active compounds. The chemical composition and active molecules of plant extracts have been extensively researched, and active molecules such as polysaccharides, flavonoids, alkaloids, saponins, terpenes, phenolic acids, and volatile oils have been detected. These bioactive molecules possess antioxidant, anti-inflammatory, anti-cancer, blood pressure-lowering, and blood sugar-lowering properties, among others. Some extracts also have antibacterial, antiviral, antiallergic, and analgesic properties.

Overall, plant extracts and natural compounds have an abundance of promising bioactive substances that can benefit human health and well-being. We welcome submissions of original articles, reviews, and communication. This Special Issue is supervised by Prof. Lazari Diamanto, who is assisted by our Topical Advisory Panel Member: Olga Tsiftsoglou <[email protected]> (Aristotle University of Thessaloniki).

Please note: Papers describing the effects of mixed extraction from natural origin, and substances without clear ingredients, such as complex prescription, crude extract, and herbal mixture, do not fall within the scope of IJMS.

Prof. Dr. Diamanto Lazari
Guest Editor

Manuscript Submission Information

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Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. International Journal of Molecular Sciences is an international peer-reviewed open access semimonthly journal published by MDPI.

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Keywords

bioactive substances
plant extracts
polysaccharides
flavonoids
alkaloids
saponins
terpenes
phenolic acids
volatile oils
antioxidant/anti-inflammatory/anti-cancer
blood pressure lowering
blood sugar lowering
antibacterial
antiviral
antiallergic

Published Papers (10 papers)

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Research

19 pages, 1538 KiB

Open AccessArticle

Chemical Constituents and Anticancer Activities of the Extracts from Phlomis × commixta Rech. f. (P. cretica × P. lanata)

by Michalis K. Stefanakis, Olga St. Tsiftsoglou, Pavle Z. Mašković, Diamanto Lazari and Haralambos E. Katerinopoulos

Int. J. Mol. Sci. 2024, 25(2), 816; https://doi.org/10.3390/ijms25020816 - 09 Jan 2024

Cited by 1 | Viewed by 720

Abstract

The present work is the first report on the ingredients of the P. × commixta hybrid, a plant of the genus Phlomis. So far, thirty substances have been isolated by various chromatographic techniques and identified by spectroscopic methods, such as UV/Vis, NMR, GC-MS and LC-MS. The compounds are classified as flavonoids: naringenin, eriodyctiol, eriodyctiol-7-O-β-D-glucoside, luteolin, luteolin-7-O-β-D-glucoside, apigenin, apigenin-7-O-β-D-glucoside, diosmetin-7-O-β-D-glucoside, quercetin, hesperetin and quercetin-3-O-β-D-glucoside; phenylpropanoids: martynoside, verbascoside, forsythoside B, echinacoside and allysonoside; chromene: 5,7-dihydroxychromone; phenolic acids: caffeic acid, p-hydroxybenzoic acid, chlorogenic acid, chlorogenic acid methyl ester, gallic acid, p-coumaric acid and vanillic acid; aliphatic hydrocarbon: docos-1-ene; steroids: brassicasterol and stigmasterol; a glucoside of allylic alcohol, 3-O-β-D-apiofuranosyl-(1→6)-O-β-D-glucopyranosyl-oct-1-ene-3-ol, was fully characterized as a natural product for the first time. Two tyrosol esters were also isolated: tyrosol lignocerate and tyrosol methyl ether palmitate, the latter one being isolated as a natural product for the first time. Moreover, the biological activities of the extracts from the different polarities of the roots, leaves and flowers were estimated for their cytotoxic potency. All root extracts tested showed a high cytotoxic activity against the Hep2c and RD cell lines. Full article

(This article belongs to the Special Issue Molecular Studies of Natural Compounds and Plant Extracts)

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11 pages, 3713 KiB

Open AccessCommunication

Analysis of Three Species of Cassipourea Traditionally Used for Hypermelanosis in Selected Provinces in South Africa

by Nomakhosi Mpofana, Masande Yalo, Nceba Gqaleni, Ncoza Cordelia Dlova and Ahmed A. Hussein

Int. J. Mol. Sci. 2024, 25(1), 237; https://doi.org/10.3390/ijms25010237 - 23 Dec 2023

Viewed by 582

Abstract

There is a growing demand and use of herbal cosmetics for skin purposes due to their perceived safety when applied to the skin. Three Cassipourea species commonly known as “ummemezi” are used interchangeably by women in rural areas of Eastern Cape and KwaZulu-Natal provinces to treat hypermelanosis as well as sun protection. We conducted a phytochemical comparison of three Cassipourea species; Cassipourea flanaganii (Schinz) Alston, Cassipourea gummiflua Tul. verticillata (N.E.Br.) J. Lewis and Cassipourea malosana (Baker) Alston by Liquid Chromatography–Mass Spectrometry (LC-MS/MS) analysis in negative mode. The results obtained from the LC-MS/MS yielded a total number of twenty-four compounds of different chemical classes, including fatty acids, steroids, di- and tri-terpenoids, flavonoids, phenolic acids, and eighteen among them were tentatively identified. The LC-MS /MS analysis showed that the three studied Cassipourea extracts contain compounds that have anti-tyrosinase activity and consequently. The presence of these compounds, either in synergy or individually, can be attributed to the anti-tyrosinase effect. Although the traditional names of the species are used interchangeably, they are different, however, they possess similar skin-lightening properties. Despite the recent popularity of modern cosmetic products, plants continue to play an important role in the local cosmetics industry in South Africa’s Eastern Cape and KwaZulu-Natal community provinces. Full article

(This article belongs to the Special Issue Molecular Studies of Natural Compounds and Plant Extracts)

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20 pages, 4633 KiB

Open AccessArticle

Discovery of Anti-Coronavirus Cinnamoyl Triterpenoids Isolated from Hippophae rhamnoides during a Screening of Halophytes from the North Sea and Channel Coasts in Northern France

by Malak Al Ibrahim, Zachee Louis Evariste Akissi, Lowiese Desmarets, Gabriel Lefèvre, Jennifer Samaillie, Imelda Raczkiewicz, Sevser Sahpaz, Jean Dubuisson, Sandrine Belouzard, Céline Rivière and Karin Séron

Int. J. Mol. Sci. 2023, 24(23), 16617; https://doi.org/10.3390/ijms242316617 - 22 Nov 2023

Viewed by 1381

Abstract

The limited availability of antiviral therapy for severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) has spurred the search for novel antiviral drugs. Here, we investigated the potential antiviral properties of plants adapted to high-salt environments collected in the north of France. Twenty-five crude methanolic extracts obtained from twenty-two plant species were evaluated for their cytotoxicity and antiviral effectiveness against coronaviruses HCoV-229E and SARS-CoV-2. Then, a bioguided fractionation approach was employed. The most active crude methanolic extracts were partitioned into three different sub-extracts. Notably, the dichloromethane sub-extract of the whole plant Hippophae rhamnoides L. demonstrated the highest antiviral activity against both viruses. Its chemical composition was evaluated by ultra-high performance liquid chromatography (UHPLC) coupled with mass spectrometry (MS) and then it was fractionated by centrifugal partition chromatography (CPC). Six cinnamoyl triterpenoid compounds were isolated from the three most active fractions by preparative high-performance liquid chromatography (HPLC) and identified by high resolution MS (HR-MS) and mono- and bi-dimensional nuclear magnetic resonance (NMR). Specifically, these compounds were identified as 2-O-trans-p-coumaroyl-maslinic acid, 3β-hydroxy-2α-trans-p-coumaryloxy-urs-12-en-28-oic acid, 3β-hydroxy-2α-cis-p-coumaryloxy-urs-12-en-28-oic acid, 3-O-trans-caffeoyl oleanolic acid, a mixture of 3-O-trans-caffeoyl oleanolic acid/3-O-cis-caffeoyl oleanolic acid (70/30), and 3-O-trans-p-coumaroyl oleanolic acid. Infection tests demonstrated a dose-dependent inhibition of these triterpenes against HCoV-229E and SARS-CoV-2. Notably, cinnamoyl oleanolic acids displayed activity against both SARS-CoV-2 and HCoV-229E. Our findings suggest that Hippophae rhamnoides could represent a source of potential antiviral agents against coronaviruses. Full article

(This article belongs to the Special Issue Molecular Studies of Natural Compounds and Plant Extracts)

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14 pages, 2008 KiB

Open AccessArticle

Effect of Flavonoids on MCP-1 Expression in Human Coronary Artery Endothelial Cells and Impact on MCP-1-Dependent Migration of Human Monocytes

by Lea Brüser, Elisa Teichmann and Burkhard Hinz

Int. J. Mol. Sci. 2023, 24(22), 16047; https://doi.org/10.3390/ijms242216047 - 07 Nov 2023

Viewed by 864

Abstract

The monocyte chemoattractant protein-1 (MCP-1), also known as chemokine (CC motif) ligand 2 (CCL2), is involved in the formation, progression, and destabilization of atheromatous plaques. Flavonoids, found in fruits and vegetables, have been associated with various health-promoting properties, including antioxidant, anti-inflammatory, and cardioprotective effects. In the present study, the flavonoids quercetin, kaempferol, and luteolin, but not cannflavin A, were shown to substantially inhibit interleukin (IL)-1β-induced MCP-1 mRNA and protein expression in human coronary artery endothelial cells (HCAEC). At the functional level, conditioned medium (CM) from IL-1β-stimulated HCAEC caused an increase in the migration of THP-1 monocytes compared with CM from unstimulated HCAEC. However, this induction was suppressed when IL-1β-treated HCAEC were coincubated with quercetin, kaempferol, or luteolin. The functional importance of MCP-1 in IL-1β-induced monocyte migration was supported by experiments showing that neutralization of MCP-1 in the CM of IL-1β-treated HCAEC led to a significant inhibition of migration. In addition, a concentration-dependent induction of monocyte migration in the presence of recombinant MCP-1 was demonstrated. Collectively, the flavonoids quercetin, kaempferol, and luteolin were found to exert potential antiatherogenic effects in HCAEC, challenging further studies with these compounds. Full article

(This article belongs to the Special Issue Molecular Studies of Natural Compounds and Plant Extracts)

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23 pages, 3407 KiB

Open AccessArticle

The Antioxidant and Immunomodulatory Potential of Coccoloba alnifolia Leaf Extracts

by Luciana Fentanes Moura de Melo, Jefferson da Silva Barbosa, Maria Lúcia da Silva Cordeiro, Verônica Giuliani de Queiroz Aquino-Martins, Ariana Pereira da Silva, Weslley de Souza Paiva, Elielson Rodrigo Silveira, Déborah Yara A. Cursino dos Santos, Hugo Alexandre Oliveira Rocha and Kátia Castanho Scortecci

Int. J. Mol. Sci. 2023, 24(21), 15885; https://doi.org/10.3390/ijms242115885 - 01 Nov 2023

Viewed by 1191

Abstract

Oxidative stress has been associated with different diseases, and different medicinal plants have been used to treat or prevent this condition. The leaf ethanolic extract (EE) and aqueous extract (AE) from Coccoloba alnifolia have previously been characterized to have antioxidant potential in vitro and in vivo. In this study, we worked with EE and AE and two partition phases, AF (ethyl acetate) and BF (butanol), from AE extract. These extracts and partition phases did not display cytotoxicity. The EE and AE reduced NO production and ROS in all three concentrations tested. Furthermore, it was observed that EE and AE at 500 μg/mL concentration were able to reduce phagocytic activity by 30 and 50%, respectively. A scratch assay using a fibroblast cell line (NHI/3T3) showed that extracts and fractions induced cell migration with 60% wound recovery within 24 h, especially for BF. It was also observed that AF and BF had antioxidant potential in all the assays evaluated. In addition, copper chelation was observed. This activity was previously not detected in AE. The HPLC-DAD analysis showed the presence of phenolic compounds such as p-cumaric acid and vitexin for extracts, while the GNPS annotated the presence of isoorientin, vitexin, kanakugiol, and tryptamine in the BF partition phase. The data presented here demonstrated that the EE, AE, AF, and BF of C. alnifolia have potential immunomodulatory effects, antioxidant effects, as well as in vitro wound healing characteristics, which are important for dynamic inflammation process control. Full article

(This article belongs to the Special Issue Molecular Studies of Natural Compounds and Plant Extracts)

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22 pages, 4903 KiB

Open AccessArticle

A Comparative Study between Onion Peel Extracts, Free and Complexed with β-Cyclodextrin, as a Natural UV Filter to Cosmetic Formulations

by Mariana A. Messias, Sara M. Ferreira, Loleny Tavares and Lúcia Santos

Int. J. Mol. Sci. 2023, 24(21), 15854; https://doi.org/10.3390/ijms242115854 - 01 Nov 2023

Viewed by 1817

Abstract

The growing concern regarding the adverse effects of synthetic UV filters found in sunscreens has spurred significant attention due to their potential harm to aquatic ecosystems and human health. To address this, the present study aimed to extract and microencapsulate sensitive bioactive compounds derived from by-product onion peel (OP) by molecular inclusion using β-cyclodextrin as the wall material. Identification and quantification of bioactive compounds within the extract were conducted through high-performance liquid chromatography (HPLC-DAD) analysis, revealing quercetin and resveratrol as the primary constituents. The photoprotection capacity, evaluated by the sun protection factor (SPF), revealed a protection factor comparable to the value for a synthetic UV filter. The produced microparticles presented high antioxidant capacity, significant photoprotection capacity, encapsulation efficiency of 91.8%, mean diameter of 31 μm, and polydispersity of 2.09. Furthermore, to comprehensively evaluate the performance of OP extract and its potential as a natural UV filter, five O/W emulsions were produced. Results demonstrated that microparticles displayed superior ability in maintaining SPF values over a five-week period. Photoprotection evaluation–skin reactivity tests revealed that both extract and microparticles absorb UV radiation in other regions of UV radiation, revealing their potential to be used as a natural UV filter to produce a sustainable and eco-friendly value-added sunscreen. Full article

(This article belongs to the Special Issue Molecular Studies of Natural Compounds and Plant Extracts)

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10 pages, 1321 KiB

Open AccessArticle

Natural Compounds Purified from the Leaves of Aristotelia chilensis: Makomakinol, a New Alkaloid and the Effect of Aristoteline and Hobartine on Na_V Channels

by Rebeca Pérez, Claudia Figueredo, Viviana Burgos, Jaime R. Cabrera-Pardo, Bernd Schmidt, Matthias Heydenreich, Andreas Koch, Jennifer R. Deuis, Irina Vetter and Cristian Paz

Int. J. Mol. Sci. 2023, 24(21), 15504; https://doi.org/10.3390/ijms242115504 - 24 Oct 2023

Viewed by 1048

Abstract

Aristotelia chilensis or “maqui” is a tree native to Chile used in the folk medicine of the Mapuche people as an anti-inflammatory agent for the treatment of digestive ailments, fever, and skin lesions. Maqui fruits are black berries which are considered a “superfruit” with notable potential health benefits, promoted to be an antioxidant, cardioprotective, and anti-inflammatory. Maqui leaves contain non-iridoid monoterpene indole alkaloids which have previously been shown to act on nicotinic acetylcholine receptors, potassium channels, and calcium channels. Here, we isolated a new alkaloid from maqui leaves, now called makomakinol, together with the known alkaloids aristoteline, hobartine, and 3-formylindole. Moreover, the polyphenols quercetine, ethyl caffeate, and the terpenes, dihydro-β-ionone and terpin hydrate, were also obtained. In light of the reported analgesic and anti-nociceptive properties of A. chilensis, in particular a crude mixture of alkaloids containing aristoteline and hobartinol (PMID 21585384), we therefore evaluated the activity of aristoteline and hobartine on Na_V1.8, a key Na_V isoform involved in nociception, using automated whole-cell patch-clamp electrophysiology. Aristoteline and hobartine both inhibited Nav1.8 with an IC₅₀ of 68 ± 3 µM and 54 ± 1 µM, respectively. Hobartine caused a hyperpolarizing shift of the voltage-dependence of the activation, whereas aristoteline did not change the voltage-dependence of the activation or inactivation. The inhibitory activity of these alkaloids on Na_V channels may contribute to the reported analgesic properties of Aristotelia chilensis used by the Mapuche people. Full article

(This article belongs to the Special Issue Molecular Studies of Natural Compounds and Plant Extracts)

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14 pages, 3339 KiB

Open AccessArticle

Silibinin Downregulates Types I and III Collagen Expression via Suppression of the mTOR Signaling Pathway

by Sooyeon Choi, Seoyoon Ham, Young In Lee, Jihee Kim, Won Jai Lee and Ju Hee Lee

Int. J. Mol. Sci. 2023, 24(18), 14386; https://doi.org/10.3390/ijms241814386 - 21 Sep 2023

Viewed by 1016

Abstract

Keloid scars are fibro-proliferative conditions characterized by abnormal fibroblast proliferation and excessive extracellular matrix deposition. The mammalian target of the rapamycin (mTOR) pathway has emerged as a potential therapeutic target in keloid disease. Silibinin, a natural flavonoid isolated from the seeds and fruits of the milk thistle, is known to inhibit the mTOR signaling pathway in human cervical and hepatoma cancer cells. However, the mechanisms underlying this inhibitory effect are not fully understood. This in vitro study investigated the effects of silibinin on collagen expression in normal human dermal and keloid-derived fibroblasts. We evaluated the effects of silibinin on the expressions of collagen types I and III and assessed its effects on the suppression of the mTOR signaling pathway. Our findings confirmed elevated mTOR phosphorylation levels in keloid scars compared to normal tissue specimens. Silibinin treatment significantly reduced collagen I and III expressions in normal human dermal and keloid-derived fibroblasts. These effects were accompanied by the suppression of the mTOR signaling pathway. Our findings suggest the potential of silibinin as a promising therapeutic agent for preventing and treating keloid scars. Further studies are warranted to explore the clinical application of silibinin in scar management. Full article

(This article belongs to the Special Issue Molecular Studies of Natural Compounds and Plant Extracts)

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28 pages, 7986 KiB

Open AccessArticle

Biological Activities of Ceratonia siliqua Pod and Seed Extracts: A Comparative Analysis of Two Cretan Cultivars

by Dafni-Alexandra Kavvoura, Michalis K. Stefanakis, Dimitris Kletsas, Haralambos E. Katerinopoulos and Harris Pratsinis

Int. J. Mol. Sci. 2023, 24(15), 12104; https://doi.org/10.3390/ijms241512104 - 28 Jul 2023

Cited by 3 | Viewed by 1246

Abstract

Ceratonia siliqua L., commonly known as the carob tree, appears in most Mediterranean countries, often cultivated for the collection of its fruits to be used as food for humans and animals. This study was aimed at the phytochemical characterization of two common Cretan C. siliqua cultivars and the biological evaluation of deseeded pod and seed extracts regarding their putative use in cosmetics. Gas and liquid chromatographic techniques were used to assess their essential oil, fatty acid, and carbohydrate profiles. Cell-free assays, including free-radical scavenging; the inhibition of tyrosinase and collagenase; the blocking of advanced glycation end product (AGE) formation; along with assays in human skin fibroblast cultures, i.e., reactive oxygen species suppression, glutathione stimulation, and protection from oxidative stress and from ultraviolet (UVB) radiation, were also used. Extracts from both cultivars were found to possess antioxidant capacity, tyrosinase- and collagenase-inhibitory activities, an ability to block glucose-induced AGEs, and in certain cases, UVB absorbance and photoprotective activities. Seed extracts were in general more active, while the use of 30% aqueous methanol seemed to be more efficient than n-hexane for extraction. Serial partition of the most active extracts resulted in fractions with enriched biological activities. These properties make Cretan carob extracts and their fractions suitable candidates for use in cosmetics. Full article

(This article belongs to the Special Issue Molecular Studies of Natural Compounds and Plant Extracts)

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22 pages, 5145 KiB

Open AccessArticle

Prevention of UVB Induced Metabolic Changes in Epidermal Cells by Lipid Extract from Microalgae Nannochloropsis oceanica

by Anna Stasiewicz, Tiago Conde, Agnieszka Gęgotek, Maria Rosário Domingues, Pedro Domingues and Elżbieta Skrzydlewska

Int. J. Mol. Sci. 2023, 24(14), 11302; https://doi.org/10.3390/ijms241411302 - 11 Jul 2023

Cited by 4 | Viewed by 1205

Abstract

The exposure of skin cells to UV radiation leads to redox imbalances and inflammation. The present study investigates a lipid extract obtained from the microalga Nannochloropsis oceanica as a potential protector against UVB-induced disturbances in human keratinocytes. The findings of this study show that the Nannochloropsis oceanica extract significantly inhibits UVB-induced cell death while concurrently decreasing the activity of pro-oxidative enzymes (xanthine and NADPH oxidase) and reducing the levels of ROS. Furthermore, the extract augments the activity of antioxidant enzymes (superoxide dismutases and catalase), as well as glutathione/thioredoxin-dependent systems in UVB-irradiated cells. The expression of Nrf2 factor activators (p62, KAP1, p38) was significantly elevated, while no impact was observed on Nrf2 inhibitors (Keap1, Bach1). The antioxidant activity of the extract was accompanied by the silencing of overexpressed membrane transporters caused by UVB radiation. Furthermore, the Nannochloropsis oceanica extract exhibited anti-inflammatory effects in UVB-irradiated keratinocytes by decreasing the levels of TNFα, 8-iso prostaglandin F2, and 4-HNE-protein adducts. In conclusion, the lipid components of Nannochloropsis oceanica extract effectively prevent the pro-oxidative and pro-inflammatory effects of UVB radiation in keratinocytes, thereby stabilizing the natural metabolism of skin cells. Full article

(This article belongs to the Special Issue Molecular Studies of Natural Compounds and Plant Extracts)

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